


The Apprentice

by Pain_And_Friendly_Advice



Series: Reapers [2]
Category: Villainous (Cartoon)
Genre: Blood and Gore, Breeding Kink, Dubious Consent, Explicit Sexual Content, F/F, F/M, Multi, Murder, Oviposition, Rape/Non-con Elements, Service Kink, Some Bondage, Torture, Violence, maybe even more let's just see where this goes
Language: English
Status: In-Progress
Published: 2018-07-28
Updated: 2018-08-19
Packaged: 2019-06-17 11:49:15
Rating: Explicit
Warnings: Graphic Depictions Of Violence, Rape/Non-Con
Chapters: 7
Words: 7,342
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15460731
Author URL: https://archiveofourown.org/users/Pain_And_Friendly_Advice/pseuds/Pain_And_Friendly_Advice
Summary: You made a fatal mistake while performing your 'grim reaper' duties. Now your only options are to serve Black Hat or return to hell. Well... tough experiences are supposed to build character, right?Dark sequel to "Psychopomp"





	1. Pretty Little Head

**Author's Note:**

> This is one of two parallel sequels to my fic "Psychopomp". Please give that a read, otherwise this won't make a lot of sense.

The room was much darker when you came back around. With a drawn out groan, you sat up and grasped your aching head. You desperately needed something to eat, you finally realized. How long had it been since you’d had anything? Yes, you weren’t human and could go much longer without sustenance, but you still needed food.

  
You slid out of bed and, after a brief visit to the nearby bathroom, ventured out into the dimly lit hallway. The place was quiet, and you honestly had no idea what to expect when you rounded one corner after another. Had the layout changed since you were here last?

  
After a while, you came across a room with the lights on. You peeked through the open door to find just what you were hoping for- a kitchen. The room looked more like the back of a fancy restaurant than a place to scavenge for snacks, but that didn’t matter. You weren’t exactly feeling picky.

  
You scurried over to the enormous refrigerator and opened the door, and right away found a bowl of fruit. You chose an apple, leaning against the counter and taking a bite. Much as you would’ve liked to simply enjoy the first food you’d had in days, you just had too much on your mind. 

  
Would it have been better if you’d stayed at Black Hat’s home? Would you have to worry about seeing him again after your sudden departure? At first you didn’t think so; you owed him nothing. But that was the _exact_ thought you’d had about White Hat, and look where you were.

  
Perhaps Black Hat wouldn’t find it worth his time to pursue you. Why would he even see the need?

  
“You really fucked up.” A voice answered the internal question for you. Spinning around, you saw a young man approaching you from the hallway. 

  
Your first thought was that he was astonishingly handsome; he had short black hair, green eyes, and deliberate stubble along a very strong jawline. The second thought, was that you’d seen him before. Glancing down at his heavily bandaged left hand confirmed this- he was the man White Hat had been _disciplining_ the other morning.

  
You only stared at him questioningly with a mouth full of fruit.

  
“It had to be done,” He said in a hushed tone, having noticed your gaze on his injured hand. “He trusts me. _You_ should have stayed away.”

  
“I didn’t exactly walk myself back here…” You replied, swallowing and placing the bitten apple on the counter. “Who are you?”

  
“My name’s Mason. Let’s just say you and I are from the same... _neighborhood_.” He said, moving even closer and standing over you in an intimidating sort of way. “But I moved out sooner, and my job is more important than yours.”

  
You gulped, feeling like the biggest loser to ever walk the earth. The way he was glaring at you, you may as well have been. There were certain instincts that came with being a demon. One of which involved dropping to the ground like a wounded animal under the will of a stronger being. You fought this out of stubbornness.

  
“What should I do, then?” You asked steadily.

  
He leaned in closer, mere inches from your face at this point. Though you tried so hard to remain firm, a whimper escaped you. What was _with_ this guy…? You had held up just fine in front of two more powerful eldritch demons, after all…  
  


“Leave.” He said plainly. “This place- this aberrant floating landmass - _relies_ on prolonged suffering. I’m going to assume that no one of significant experience was present when you performed your little _magic trick_? Any monster worth their salt would have sensed the necessity of widespread distress on this island the very moment they got here.”

  
You felt so completely oppressed by his glare that you hadn’t noticed yourself crouching closer and closer to the kitchen floor. You half-hoped he would just squash you like a bug and be done with it.

  
Mason straightened his posture but didn’t break eye contact. “I suppose the simplest way to say it, would be this: You’re not needed here. Or anywhere. Remove yourself before I disassemble you personally.”

  
“Y-You can’t do that!” You blurted out as he left the room without another glance at you. He didn’t have to respond; you could feel in every fiber of your being that he _could_ strip you of your purpose and by extension, your existence. 

  
“Tick tock, bitch.” …And indeed, he just had.  
  


 

* * *

  
  
Six hours: roughly the amount of time your pitiful form would be allowed to linger. You had a few options, but latched onto the first plan of escape you could think of. Returning to the bedroom where you’d been staying, you locked yourself in and ran it over in your mind a few frantic times. 

  
White Hat _might_ let you stay. You suspected he would, the way he calmly reacted to your mistakes earlier. If it weren’t for Mason’s threat to destroy you, you might’ve considered this option more carefully. You were eager to get the hell away from him. 

  
So then, who else might have the authority to prolong your sad presence on this plane of existence? 

  
While pacing the room, you noticed with a touch of relief that some clothes had been left for you. Not that you wouldn’t flee just as quickly while wearing that neon pink ‘kill me’ flag from Clemencia.

  
Oh, what a shameful affair this was all shaping up to be. You had actually been glad to see her and Slug earlier, too. You quickly donned what had been left: jeans, a dark grey T-shirt, and your coat. But of course, not before slipping into the pair of panties with a note that simply said ‘Try not to lose these’.  
  
You wanted to laugh, you really did. The angry little she-beast inside you raged against the urgency to escape. You’d have loved to turn that bastard Mason inside out. But you knew that if you didn't get out of there, you'd never even get the chance.


	2. Unsafe Safe

**Summary for the Chapter:**

> new Black king  
> obey, obey, obey

The door rattled before you could reach for the lock. 

  
“Are you all right in there?” Came White Hat’s voice. You froze with icy terror, even though he sounded as amiable as ever. “Fear has a very distinct odor, you know.”

  
“Yes, I’m fine!” You said, forcing a manic grin as though you could convince yourself with it. “I just… was wandering the house and I… stumbled across Clemencia’s… wardrobe…”

  
“Hrmm.” He replied through the door. “Yes, I suppose that might elicit fear in some folks…” 

  
You were both quiet for a moment as you took long, deliberate breaths to calm yourself. 

  
“Very well then, I suppose I’ll leave you to your… overwhelming repulsion. But you really should try to lighten up, darling.” He said airily, and you heard his footsteps slowly move away from the door. 

  
You wanted to stop him. Maybe he could have done something. But Mason’s words hung in your mind: _“He trusts me. Tick tock, bitch.”_

  
You stomped over to the balcony with fresh indignation. Opening the door and looking down, you estimated the distance to the ground to be… 5 stories, maybe? There was a good sized sycamore below, however. Wonderful… could you spare a few broken bones? Yeah, fine, why not?! 

  
Not taking the time to fret over details, you hoisted yourself over the railing and dropped quickly through the night air, into the waiting branches below. You appreciated the smooth bark as you untangled your limbs and dropped like a rock to the sidewalk. At least you wouldn’t have an ass full of splinters.

 

* * *

  
  
The tree had been merciful; you only had several bumps and bruises, and maybe a sprained wrist. 

  
You let out a shaky, pained breath when Black Hat’s manor finally came into view. After scurrying away into the city with bare feet and sore everything, you were pleasantly surprised at how quickly you’d managed to find it. You made your way toward it, checking yourself again for any clinging leaves or twigs.

  
The front gate was open, and there was a light on above the main doors. Taking that to be as good an invitation as any, you strode up the walkway, glancing behind and hoping no one was watching. 

  
The doors flew open to reveal the hat himself, a sharp-toothed grin painted unnaturally on his face. “Welcome back, my little grub!” He said magnanimously. “ _Come in, come in_ … get up to much _mischief_ while you were out? _Well_?” 

  
You hurried inside, closing the doors behind you. “Ah… no, sir?” Was all you could muster. The conflicting emotions regarding this particular eldritch returned as he stood over you. In this situation… better to kiss his ass.

  
“No? Well you must have done something,” He cackled, looking expectantly at you. He knew. Of course he did, he was Black Hat, and Black Hat just… knows. He was _waiting_ for you to kiss his ass in exchange for your continued existence.

  
“Oh. Right…” You exhaled shakily, wondering whether you should kneel or something. “I’ve been… relieved of my duties. Turns out there’s another like me already here, so… I…” You trailed off as his gaze seemed to becoming at you from all directions. You shrunk back. 

  
“Another?” He grimaced. “Would you be referring to the self-important little bastard my _counterpart_ keeps as a lap dog…?”

  
“Um… Mason. Yes, for lack of a better term he ah… fired me?”

  
“WELL he clearly didn’t do a very good JOB, considering you’re HERE sucking WIND and clearly NOT BURNING AT ALL -! WAIT.” He regarded you with a single, bulging red eye. “That feckless _roach_ has authority over you…?”

  
“Y-yes… I mean, no! Not anymore.” You swallowed. May as well come out and say it, even if he was already aware of the truth. “I can only serve you now, Lord Black Hat. Or… return to the depths.”

  
“Hmmmm yessss… I do like the way the truth sounds on your lips…” He hissed, placing a gloved hand under your chin. “And you would serve me? Or perish…?”

  
You shivered, unable to help yourself as your gaze met his. “My fate is for you to decide…” You squeaked out.

  
He let out a bellowing laugh that rattled your bones. “Very good, little grub!” He cackled, grabbing you up in one arm and carrying you off like a nervous little football.

  
Regret would be a waste at this point, so you shoved it aside. Yes, you were likely to experience a new brand of hell at Black Hat’s claws, but perhaps it was for the best. Perhaps you could learn from him. 


	3. Questions

**Summary for the Chapter:**

> Best keep that mumbo jumbo to yourself, ya hippie.

Black Hat had carried you to his office and dropped you near his desk, all the while crooning about how _thrilled_ he was to have a displaced little imp crawling to his doorstep for guidance, and how exciting it was that he could dole out his punishments on something that might actually _survive_ a while.

  
You just sat on the floor for a moment, the urge to fight this monster being thoroughly doused by the knowledge that he essentially owned you now. He fell silent after a while, prompting you to look up at him sitting behind his desk. 

  
“It shall never be said that the great Black Hat does not pay what is due…” He grumbled. 

  
You thought that was a warning, but he looked somewhat indignant as he motioned for you to stand up. 

  
“I suppose I owe you a spot of gratitude for clearing up the… _infestation_ in my home.” He said, opening a desk drawer and rifling through the contents. “The other psychopomp refused to assist… I’d have had his ass on my wall if he didn’t run off and hide behind that _impostor_ …” 

  
“Oh, right. The… vortex.” You said quietly, wondering what he could be looking for in there. “I should tell you the reason-“

  
“Yes, yes, Flug and his bloody experiments.” Black Hat snapped. “Your first order is to assure another plague does not come about. I greatly value peace and quiet in my home.”

  
“Y-yes sir…” Great, your first order was a tall one. However, he didn’t seem to view your previous actions as the debacle they turned out to be, so you decided to hold your tongue.

  
“You may consider _this_ -“ He slapped a form onto the desk and pushed it toward you. “…My gratitude.”

  
It was a contract which, upon quickly looking the document over, you found outlined your agreement to subjugation. You didn’t bother asking to read it first. The options were _this_ , or… disincorporation. When he handed you a quill- how avant-garde - you didn’t hesitate to sign the contract.

  
“Very good. Now,” He purred. “Flug has a _guest_ , if you will. Do be sure there are no lingering issues.”

  
He waved you away, returning the signed contract to his desk drawer. You turned and walked out of the office, remembering the way to the lab from the day before. Once you reached it, you immediately spotted Flug slouching over a messy desk in the corner, a large blue-furred ursine sitting beside him. 

  
The bear turned and tilted his head, staring at you with huge, adorable eyes. You carefully approached the doctor, smiling at the creature and raising your hands to show you meant no harm. Even though you couldn't really feel threatened by something with a yellow flower sprouting from its head.

  
“Hey, ah… are you all right?” You asked, stopping behind Flug. “Who’s this? I didn’t see him last time I was here…”

  
“… 5.0.5.. He hibernates.” Flug responded in monotone. 

  
“Okay, but… it’s summer…” 

  
He just shrugged. You winced, reaching out to touch his shoulder. “Um… Doc? Are you all right?” You asked.

  
He seemed to slowly come to life at your touch, turning to stare at you from behind his huge goggles. “Wait… you’re actually here.”

  
That was an alarming statement. “Yes, and… I’ll be here for the foreseeable future.” You said quietly. “I work for Black Hat now.” 

  
This admission was more for your own benefit than his. You hadn’t quite come to terms with the way things had changed in only a few hours. To your surprise, your words seemed to perk him up a bit. 

  
“Really…? You’re staying?” He asked, getting to his feet. 

  
“Y-Yes…?” 

  
You squealed with surprise when he grabbed you up in a tight hug. “That’s so… so…” He squeezed you harder. “Wonderful! Now the Boss man will have someone else to torment!”

  
“…Yep…” You wheezed. Well, he wasn’t _wrong_.

  
5.0.5. got up and joined Flug in squishing you. “Um… so…” You gasped. “The Boss said you have… a guest?”

  
“Oh! Yes, that’s correct!” He replied, releasing you. “You can assist me! I’ve not had the opportunity to work closely with a _demoness_ before! Though I suppose Demencia does come close…”

  
You stared at him as though he were a bit of roadkill that just magically came back to life. These manic episodes of his might take some getting used to. 

  
“You know what I am?” You asked, interrupting his excited ranting. 

  
“Indeed! The Boss man told me. I’ve never subscribed to the idea of there even being such a place as hell, but I _would_ like to know more about it, considering that may be my destination after death, provided Jefecito doesn’t consume my soul before I- Oh! That reminds me…” He leaned in close and dropped his voice. “What did _you_ do to land in such a place…?”

  
You found yourself waiting a couple of seconds to be sure he was done talking before you responded. “Oh, haha… I couldn't tell you if I wanted to. I have no memory of being alive before then…”

  
He raised an eyebrow. How did he even do that with the bag. 

  
“Besides, it’s irrelevant.” You finished. This piqued his curiosity even more. 

  
“Please elaborate.” He said eagerly, before diving into an open desk drawer to find note-taking implements. 

  
Oh boy, how could you even begin to describe what was probably a secret of the universe? You hadn’t even bothered thinking about it since you were a wee little imp. How had it been explained to you, again..?

  
There was a randomness to it, at least in this word. Similar to being born, in that you just popped into that existence- having had no knowledge of what you would be in terms of species, appearance, or geographical location. Maybe there was a predisposition to those who popped into hell. Maybe some higher power passed judgement. 

  
Maybe everything just had a great complexity to it- endless incomprehensible shades of grey between the black and white we think we can comfortably understand.

  
None of it was for puny insects like us to know.

  
You waited for a response once you’d finished talking. Flug stared at you for several drawn out moments, 5.0.5. beside him, mirroring his dazed expression. You wondered how much the bear actually understood.

  
“That is…” He took a slow, drawn-out breath. “The most beautiful way I’ve ever heard the phrase ‘I don’t know’ uttered.”

  
You just stared back at him in silence.

  
“You should know that I appreciate brevity a great deal. Now-!” He loudly clapped his hands together. “Let’s go check on our guest, shall we?”


	4. Mercy

**Notes for the Chapter:**

> This is considerably less violent than I'd originally planned... tbh I was more interested in writing about Flug being smug/scary LOL so the graphic stuff will happen later on.
> 
> Also there are brief references to other fandoms here, but it's not necessary to understand them for things to make sense.
> 
> TW: BLOOD, death

5.0.5. wandered off as you were led by Dr. Flug into another room, which seemed to glow as harsh lights bounced off every flawlessly clean surface. Against the back wall hung a row of glass cabinets, above a silver-colored sink and counter which all looked meticulously polished. Inside the cabinets were various containers and shiny implements… Everything about this place was cold and perfect. 

  
Perhaps you’d have been more impressed, had your attention not been grabbed by a naked and unconscious woman strapped to a shiny porcelain coroner’s table.

  
The surprise lasted only a second; what else were you expecting? “This table is beautiful,” You commented, following him to the center of the room. “Is it an antique?”

  
He was absolutely thrilled with your response to all this. “Yes, it is! I had to add the restraints myself, of course, but it was worth it! So stylish and functional!” He swooned, throwing an arm across your shoulders. “At last, someone who appreciates it!”

  
You smirked. His joy was almost palpable, the silly fucker. He guided you over to a standing cabinet in one corner of the room, where several clean white coats were stored. 

  
“Here you are,” He smiled and held a coat up for you as you slid your arms into it. “Perfect! Now, once the subject awakens, we can get started. How familiar are you with medical implements?”

  
“Awakens…?” You asked, disregarding his question.

  
“Yes, the primary objective is to obtain information. I’ll be doing the majority of the work, so just do as I instruct, all right?”

  
You nodded, following him back towards the table. The woman seemed like she was struggling to come around, groaning quietly and squirming against her restraints. You didn’t bother asking about who she was, you figured if it was relevant to your duties Flug would have told you.

  
He hummed a tune, busying himself with cleaning and examining a number of sharp instruments on the counter nearby. “I really am glad you’re here to stay.” He said after a few minutes. “And, well… not only because you’re someone to share in the Boss man’s… _harassment_ …”

  
“Yeah?” You smiled, but he didn’t turn to look at you. 

  
“Y-yes, you see… It’s been a while since I’ve enjoyed sex that much… It’s actually nice to have a consenting partner for a change. Still…” He turned, folding his arms and leaning back on the counter. “I think I’d enjoy tying you up sometime…”

  
“Ah… that’s why you said you never needed to be good at it…”

  
“Oh, well… yes…” He nervously rubbed at the back of his neck, glancing up at you with an anxious look.

  
“It’s okay, it doesn’t bother me.” You said. As a literal hell-spawn, it really didn’t. “And I had fun too, actually. I don’t think I’d mind being tied up… as long as I get to remain conscious.” 

  
You winked at him, and he perked back up. His cuteness made you want to just run over squash him in a hug, but a shrill gasp quickly cut into your thoughts. 

  
“Excellent, you’re awake!” The doctor chimed, hurrying over to his captive’s side as she began to struggle on the table. Her eyes were wide with terror when she saw him. 

  
“Oh no… no no, this can’t be happening…” She said, struggling even more. 

  
“Yes, it can! And it is!” Flug said, sounding rather delighted to break the news. “Lord Black Hat told me you put up quite a fight against him. I commend you, but what’s _most_ impressive is that he didn’t decide to slaughter you! A shame, however, that decision lies with me, now…”

  
Her breathing became frantic as she stared up at him. “What do you want..?” 

  
“All I need to know is who told you about the gathering.” He said sweetly, as though chatting with an old friend. “Lord Black Hat’s sacrificial ceremonies are invitation only. No gate crashing is tolerated, you understand.”

  
Her only response was rapid, terrified breathing. 

  
“So then?” Flug pressed, lifting a rather large knife so she could see it. “A person? A friend? A vague, yet menacing government agency…?”

  
She just shook her head.

  
“Hmm, perhaps a slightly less vague agency? Oh dear. Not the Office of Secret Intelligence..? ANSWER ME.”

  
You cringed a bit as his demeanor did a one-eighty. You’d hardly registered his hand move, slicing her cheek with the blade in a single swift motion. The woman only shrieked in response. 

  
“Actually,” Flug said, turning his gaze to you. “Despite my impressive collection, I often only use one implement… I kept it as a trophy but I’ve grown rather fond of it.” He set down the knife he was holding, and drew an even larger one from somewhere on his person. 

  
You stared in curious amusement. The thing was massive; a ragged-looking, saw back hunting knife. “What do you think?” He asked, sounding thoroughly pleased with himself. 

  
A look of recognition flitted across the captive’s face. “Where did you… how..?”

  
The Doctor tossed his head back and laughed, startling the captive into a fit of screaming. He slammed the knife’s broad handle down onto her chest, knocking the wind out of her and effectively silencing her screams.

  
“I’ll take that to mean it _was_ the O.S.I.” He said in monotone. “A shame. I would have hoped they’d get the idea after their ‘walking Swedish murder machine’ failed to return.”

  
She began sobbing, tears mixing with the stream of red on her one cheek. 

  
“Indeed,” He sighed. “I’ve personally seen to the end of far too many of your comrades. It wasn’t such a bore with the first few, who seemed to have some interesting information, at least.”

  
Flug then leaned back casually against the table, examining his trophy. “So then, since I have better things to be doing at the moment, I’ll make this quick, hmm? Unless you have anything interesting to share…?”

  
No response. He shrugged, and with another expert motion, nicked the woman’s neck with the blade. 

  
You recoiled at the warm spray suddenly drenching your face. Flug laughed mischievously as you wiped at your face. 

  
“Warn me next time you’re gonna do that...” You sputtered. 

  
“Sorry,” He said sweetly over the horrific gurgling that now filled the room. “But that is a good look on you. Very becoming.”

  
“Same to you,” You smirked at the blood decorating his bag and goggles. You waited for the room to fall silent before speaking again.

  
“That was merciful of you…” You said quietly.

  
“Mm. I understand exsanguination is one of the easiest ways to die.” He said, wiping the blade on his jeans and returning it to its hiding place. 

  
“I take it these interrogations are a regular thing?” 

  
“More or less.” Flug said, walking over to a small door half way up one of the walls and opened it. “The Boss man usually brings captives for me to deal with, and there are a lot of people foolish enough to cross him.”

  
“An incinerator…?” You commented, a little surprised. “What, he doesn’t eat people?”

  
“Not so much anymore,” Flug said while a metal slab emerged from the door with a mechanical droning sound. “All right, help me move that…”


	5. Everywhere

**Notes for the Chapter:**

> tw: mentions of blood, torture
> 
> hold on to your udders folks things are just about to get kinky

It took little effort between the two of you to get the corpse off the table and into the incinerator. The real work was going to be getting all the blood cleaned up.

  
“This chaos leads me to believe your doctorate isn’t in medicine…” You teased. 

  
“Well, not _technically_ …” He chuckled. “I studied for a while, but never felt inclined to pursue a degree, given how hard my professors pushed the hippocratic oath…”

  
“Oh, okay. So you just really like making messes.” 

  
“…That is correct.”

  
You laughed, looking down at your blood-soaked clothing. What depths of depravity you were exploring… and you’d only just started working here. 

  
“Well done.” Came a growl from the doorway. You both startled, turning to see Black Hat looming at the edge of the blood puddles. “The wretch is dead and her withering soul is nowhere to be seen.”

  
He directed his oppressive gaze at you and grinned. “And look, it would seem you don’t mind getting your hands dirty for me. Very good, my pet.”

  
Flug busied himself with lighting the incinerator as Black Hat waved you over. “Come here. I believe a reward is in order.”

  
“Well, actually…” You obediently scurried over to him, but he cut you off with a gloved hand around your throat. 

  
“No? Would a punishment suit you better?” 

  
You just squeaked as he lifted you off the floor. Truthfully, you hadn’t done anything. The fact that death came quickly and easily meant you hadn’t needed to. Best not to say anything more, though…

  
“Flug, clean this up and have the report on my desk in an hour.” Black Hat barked, dropping you. You slipped a little in the blood, but managed to stay standing.

  
“And you,” Black Hat continued. “I’ll be entertaining tomorrow evening. We need to have you _presentable_.”

 

* * *

  
  
Black Hat led you out of the laboratory and into the main house- but not before ordering you to leave your bloodied clothes for Flug to incinerate. He said something about adoring human blood in many situations, but certainly not staining the carpet. 

  
You followed close behind him, completely nude and cradling your breasts from the cold air that pervaded the entire manor. Most of the time you wouldn't really mind traipsing about, butt naked, however the chill effectively made you feel exhausted in your bones.

  
This fact wasn't helped by the bath your caring employer had oh so thoughtfully drawn for you. Ice- _fucking_ \- cold, of course. As you hurried into the bath to clean the dried blood on you, he carried on about the gathering he would be hosting.

  
“A great many of my associates are of demonic origin,” He said, watching you carefully from beside the tub as he removed his gloves and long coat. “So your arrival comes at a most opportune time…”

  
He paused, rolling up his shirt sleeves. “You might say that, for a being like myself, having a hell-born servant as acceptably competent as yourself is quite a status symbol. You missed a spot, my dear.”

  
He placed a clawed hand on your head and suddenly forced you backward into the tub. You struggled to keep from inhaling water as he held you there for several seconds, before allowing you to resurface and gasp for air.

  
“But something occurred to me,” He continued. “What would be even better than simply _proclaiming_ my ownership…?”

  
With no warning, he forced you underwater again, and you got a lungful of red-tinted water this time. 

  
“There are plenty of ways to stake claim to one’s minions…” He kept talking, as you coughed and sputtered. “So I’ve been asking myself. Should I have you branded?”

  
Under the water you went, feeling like your lungs were full of ice.

  
“Or bridled, perhaps?”

  
Back down again. You were seeing spots. 

  
“Chained at my side like a trophy pet?”

  
Once more. Closer to unconsciousness.

  
“But then I thought, oh! What better method to showcase your obedience than simply scent marking you?”

  
He released you and allowed you to get some air. “After all, a _truly loyal_ servant wouldn’t force their master’s hand toward such acts. Don’t you agree?”

  
You’d draped yourself over the side of the tub to keep from weakly slipping back underwater. “Y-yes… Thank you… Lord Black Hat…” 

  
He smirked and lifted you out of the tub by your horns. No one had done that to you before, and it was an uncomfortable sensation. 

  
“… Might consider having these polished…” He muttered to himself, lowering you onto your feet. “Dry yourself off, then come to my office. And do be quick about it.”

  
He retrieved his coat and gloves from the bathroom counter and, flashing you a malicious grin, swept out of the room. 


	6. Cold

**Notes for the Chapter:**

> tw: demon sex, body horror, tentacles

You weren’t exactly in a rush to towel off after that. True, you were a demon and had been for some time, but the concept of scent marking among members of your kind was murky. You supposed there was a chance this wasn’t going to be _entirely_ horrible… and it _was_ awfully gracious of your new master to decide against branding you.

  
Once you dried off, you ventured back out into the hallway and headed silently toward Black Hat’s office. You still had no clothes, and decided against wrapping up in a towel; for some reason you thought that might annoy him. You felt tired, cold, and numb in more ways than one, and although nervous about what awaited you, you were eager to be finished.

  
“Close the door,” He ordered once you entered the room. 

  
You did as instructed and quietly approached him where he was sitting behind his desk. He hadn’t bothered to don his gloves and coat again, after nearly drowning you a moment ago. You didn’t say anything, feeling your fatigue slowly worsening in the exceptionally chilly office. 

  
Glancing up at Black Hat, you saw a look of disapproval, and immediately straightened your posture. Granted, that could have just been his default expression.

  
“Please, tell me what to do…” You murmured, feeling lost.

  
His signature toothy grin returned to this face. “You mean you don’t know how this goes?”

  
You shook your head, feeling especially puny under his predatory gaze. He waved you over with one clawed hand. Trying hard to maintain a calm facade, you moved to his side and he rose from his chair. 

  
“I am the best mentor you or anyone could ever hope to have, little grub.” He purred, delicately tracing your jawline with a claw. “However, I’m not interested in giving lectures. So I trust you’ll pay close attention, and follow my lead.”

  
It took enormous effort not to crumple at his feet. Your knees suddenly felt weak with some unholy mixture of fear and lust, hearing him speak to you like that. When he ordered you onto the desk, you didn’t hesitate, lifting yourself onto the wooden surface with your legs hanging over the edge. 

  
Black Hat sighed as he parted your legs and positioned himself between them, before unzipping his trousers. “I have preparations to make for my guests, so unfortunately this time will have to be quick…”

  
You swallowed back a gasp at the sight of his tentacle-like member squirming inches away from you. 

  
He gave a low, rumbling laugh, placing his hands on your thighs and digging his claws into the skin. You couldn’t have helped the whimper that left you when he teased your entrance with that writhing thing. It was cold. 

  
“Not to worry, there will be plenty of time to play later…” He said, before stuffing you completely in one motion. 

  
You gasped shrilly, balling your hands into fists on the desk beneath you. The sensation of being forced wide by his fat, cold cock was both exhilarating and awful. You wanted to scream when he immediately began thrusting fast and forcefully. Deciding it best to be as quiet as you could manage, you bit your lip.

  
“Mmmmmm good girl…” He growled, moving his hands to your ass and pulling you even closer to the edge of the desk while he fucked you hard against it. You had to grab onto his arms to steady yourself under his aggressive movements.

  
Your heart raced and your body felt hot, in perfect contrast to his icy touch. It had been hard to stay quiet at first, and he only seemed to get stronger as moments passed. You began to feel other, smaller tendrils emerge from him and slither around your ass and stomach as he grunted in time with his thrusting. 

  
He suddenly grabbed your shoulders and slammed your back hard onto the desk, pressing his body tightly against yours. You noticed his skin- and his hat, oddly- splitting open in various places in the form of tiny mouths, which gnashed and moaned faintly.

  
“Be still…” He warned in a hiss, his organ swelling before flooding you with a frigid torrent. 

  
Unable to hold it back, you cried out as this strange cold brought your own orgasm crashing down on you. Without thinking, you wrapped your arms around him, clinging desperately to your master’s body while yours quavered from both the chill and your climax. 

  
“Shh… let go, now.” He rumbled, pushing away once his swollen cock had reduced enough to slip out of you. “Enjoyed yourself, my pet..?”

  
You sat back up slowly, still shivering. “Y-Yes…” You whimpered, cradling your breasts and rubbing your aching nipples. 

  
You were an absolute mess after what had just happened, but he only smirked, looking as smug and poised as ever.

  
“Good. I there’s much more I wish to do to you, but for now…” He tucked himself back into his trousers and straightened himself up. “Get some rest for tomorrow. And don’t even _think_ about cleaning yourself off.”  
  


* * *

  
  
Finding your way back to the room you’d slept in before, you didn’t waste any time snuggling into the big plush bed. The warm blankets were nothing short of heavenly. 

  
Just as you were about to drift off, a shuffling sound close by startled you. You opened your eyes to see Dr. Flug leaning over you. 

  
“Didn’t mean to scare you…” He mumbled, nervously rubbing the back of his neck. “I just thought I’d check how you fared with the Boss man. Are you hurt? Any burns or open wounds?”

  
“That’s really sweet…” You said with a yawn. “No, I’m not hurt, just really cold.”

  
“Ah,” He sighed. “Yes... you’ll get used to that. Rest well, then.”

  
“Thanks, Doc…” You mumbled, quickly nodding off.


	7. Revolving Doors

You were roused by a dull sounding knock on the bedroom door. 5.0.5. shuffled to your bedside a moment later, chuffing happily when you lifted a hand to lazily pat his head. You sat up slowly, feeling a little stiff but otherwise well rested. 

  
5.0.5. held out his paws, presenting you with a neatly folded set of clothes: a short, simple black dress, black stockings, and to your horror, a pair of shiny black high heels. 

  
You donned the outfit, wanting to leave the shoes off for as long as possible. Just looking at them made your feet feel sore. After straightening your hair a bit in the bathroom, you looked over to see 5.0.5. beckoning you with a paw. 

  
You smiled and picked up the shoes, following the adorable beast out of the room. He led you up a couple of flights of stairs and down a long hallway, stopping in front of an open door.

  
“Oh, good. You’re back.” You said with a smile, stepping into Demencia’s bedroom. 

  
She grinned at you. “Yeah! Hey, that was a good one, but you won’t scare me a second time!” 

  
“Is that a challenge…?”

  
“…Maybe.” She tittered, leaping onto her unmade bed and patting the mattress in front of her. “Come sit! Black Hat told me to help you get ready for the party! And you need a lot of help.”

  
Maybe you wanted to snark back at that, but she was right. You were a fucking mess. Setting the heels down near the door and waving to 5.0.5., you strode over and sat down. 

  
While she busied herself with your hair, you glanced around at her unique decor. There were several band and movie posters, but even more hand-drawn images plastered all over the walls. Most of them depicted Black Hat and Demencia in various silly and romantic situations. You weren’t quite sure what to make of it all.

  
“Hey uh… you kind of smell.” She said after a couple of minutes.

  
“Yeah…” You sighed. “That’s the idea.”

  
“Hmm… you’re really weird. I like it though. Let’s be besties, OK?!”

  
Without another word on the matter, she started to polish the pair of horns on your head. It took her a few minutes- she said they had to be _super shiny_. You figured now would be a good time to ask some things about her, and this place you were now living.

  
She rambled extensively on Black Hat’s brilliance and perfection, how she was devoted and loyal to him and the organization, and the various murders she committed on his behalf.

  
“But sometimes it’s boring,” She said while applying a gallon of hairspray to you. “Like, he throws these parties but they’re no fun. It’s all business and no hard liquor or live sacrifices.”

  
Ah, well. That sounded tame enough. You tried to forget the ideas you’d had about this get-together previously. You kind of hoped it _would_ be boring.

 

* * *

  
  
Night had fallen, and you found yourself at your master’s side as he chatted with his guests. He was dressed especially well this evening, his impeccable outfit topped by a long black cloak

  
As it turned out, his mansion contained a ballroom. A beautiful room with high ceilings and a glorious crystal chandelier, which you quietly admired from where you stood. 

  
The night was shaping up to be dull after all, with many in attendance not speaking to each other, merely shuffling around the room in eerie silence. Few of them spared you more than a glance, and none spoke to you. 

  
There were some amongst them you recognized from various places; the news, and wanted posters for example. They were all notorious villains and crime bosses, and many were known for ruthless cruelty. You found yourself scooting ever so slightly closer to Black Hat.

  
You did, however, get a weird little sense of satisfaction when Black Hat boasted that he, the greatest master villain in existence, finally had an apprentice of proper demonic origin. He stated that most lesser demons who walked the earth were either hilariously incompetent, or too ambitious to be truly loyal. This earned you a couple of approving looks, and some appraising sniffs from the less-than-human attendees.

  
You stood there for what felt like hours, trying to keep your posture straight while silently agonizing about your sore legs and feet. Those damn heels were awful. You suspected the Boss man himself had the idea to make you wear them; he was truly a sadist, indeed.

  
You let your eyes wander the room, looking for some distraction from your discomfort. You spotted Dr. Flug in a navy-blue suit, white collared shirt, and a tie that wasn’t quite the same shade of yellow as his gloves. He was speaking animatedly with a young man boasting shiny black hair and thick, pointed glasses. This kid looked too smug for his own good, and had an obnoxious, repetitive laugh. 

  
Demencia skittered across the polished wood floor, snatching your attention away from the two nerds. She was following closely behind an angry looking penguin. You weren’t sure what surprised you more: the animal, or how well Demencia had cleaned up for the party.

  
“I need to have a private word with a client,” Black Hat said, suddenly turning toward you. “Wait here, my pet.”

  
You nodded, and he turned to walk away with a young man wearing a too-wide grin on his face, and a blood-stained blazer.

  
Standing there alone, you felt awkward and vulnerable. Perhaps you should excuse yourself to the restroom. The Boss wouldn’t be upset about _that_ , right?

  
You slipped out of the ballroom and started down the hall, realizing you didn’t exactly know your way around this house yet. You stopped when you heard footsteps behind you, and to your horror, turned to see White Hat shapeshifting out of a disguise.

  
Before you could even think of fleeing, he was upon you, gripping you in a tight hug. Too tight. You whimpered, unsure whether this was an act of affection or aggression. 

  
“Darling,” He said suddenly, loosening his grip but holding onto your arms. “Before you say anything, I want you to know I forgive you.”

  
You couldn’t have said anything if you’d wanted to, you were so shocked and confused. Maybe you felt a little guilty about taking off when he’d been so kind to you, but there was no going back for you now…

  
“It’s all right, really.” He gently stroked your cheek with a white-gloved hand. “I discovered Mason’s treachery not long after you left…”

  
He leaned in close and whispered, “The lad was just jealous.”

  
“Jealous…?” You murmured, still completely lost.

  
“I’m afraid so. I understand he even stripped you of your purpose on this plane- the incivility!” He squashed you in anther embrace. “And you were so convinced I would side with him, you fled to the only other entity with the power to keep you here..!”

  
You winced, tiny tendrils of regret wrapping around your stomach. You wrestled them back, reminding yourself what was done, was done.

  
“Well I… I can’t leave now…” You sighed, fighting the desire to hug him in return. 

  
“Indeed, he’s marked you, hasn’t he? You poor thing…” White Hat stepped back from you and with a wave of his hand, opened a portal on a nearby wall. “But, perhaps he’d consider a trade? I understand _this_ one is higher ranking…”

  
He reached through and pulled someone out: an exhausted and battered looking Mason. You choked back a growl. 

  
“I don’t know…” You said, grimacing at the sight of him. “It’s not that I wouldn’t… I mean… there was a contract…”

  
White Hat looked wounded. “Oh, I see… Creatures like us do like to uphold our word, don’t we? Not that I suspect you’d survive breaking a deal with _him_ …” 

  
He hugged you a third time, and you kind of wanted to cry.

  
“I’m dreadfully sorry, my dear. I wish you the best of luck…” He stepped toward the portal and waved. “Ta-ta then… I’ll leave this one as a gift for my _sibling_.”

  
White Hat was suddenly gone, and for a brief moment you felt horribly alone. The despair then bubbled into anger, which manifested in a heavy blow to Mason’s face. He crumpled to the ground without a sound, merely scowling in your general direction.

  
As you stood over him, you heard someone approaching. Your vision was blurry with tears of rage, so you didn’t register who it was until he spoke. 

  
“I _told_ you to wait-“ Black Hat snarled, but stopped short. “You…” He sounded both furious and excited when he addressed the man on the floor. 

  
The eldritch eagerly scooped Mason up by the neck, holding him off the ground with only one arm and seemingly no effort. 

  
“Little grub…” He said, his words bringing you back into focus. “Fetch Dr. Flug for me, will you?”


End file.
